organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Ethyl (3E)-3-[2-(4-bromo­phenyl­sulfon­yl)hydrazin-1-yl­­idene]butano­ate

aUniversity of Gujrat, Department of Chemistry, Hafiz Hayat Campus, Gujrat, Pakistan, and bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 29 April 2012; accepted 29 April 2012; online 5 May 2012)

The asymmetric unit of title compound, C12H15BrN2O4S, contains two mol­ecules (A and B), with slightly different conformations: the bromo­phenyl rings and the SO2 planes of the sulfonyl groups are oriented at dihedral angles of 50.2 (2) (mol­ecule A) and 58.24 (7)° (mol­ecule B), and the ethyl acetate groups make dihedral angles of 63.99 (19)° (A) and 65.35 (16)° (B) with their bromo­phenyl groups. In the crystal, both mol­ecules exist as inversion dimers linked by pairs of N—H⋯O hydrogen bonds, which generate R22(14) loops. The dimers are linked by C—H⋯O inter­actions.

Related literature

For a related structure, see: Uramoto et al. (1971[Uramoto, M., Ōtake, N., Ogawa, Y., Yonehara, H., Marumo, F. & Saito, Y. (1971). Acta Cryst. B27, 236-241.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H15BrN2O4S

  • Mr = 363.23

  • Triclinic, [P \overline 1]

  • a = 11.0550 (3) Å

  • b = 11.9763 (4) Å

  • c = 13.1146 (3) Å

  • α = 77.457 (1)°

  • β = 72.163 (2)°

  • γ = 73.981 (1)°

  • V = 1571.92 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.76 mm−1

  • T = 296 K

  • 0.30 × 0.15 × 0.14 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.635, Tmax = 0.650

  • 22120 measured reflections

  • 6096 independent reflections

  • 4293 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.135

  • S = 1.05

  • 6096 reflections

  • 344 parameters

  • H-atom parameters constrained

  • Δρmax = 1.27 e Å−3

  • Δρmin = −1.11 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O3i 0.86 2.46 2.909 (5) 114
N3—H3A⋯O7ii 0.86 2.36 2.8855 (13) 120
C3—H3⋯O4iii 0.93 2.53 3.450 (6) 172
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y+1, -z; (iii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

The title compound, (I) (Fig. 1), has been synthesized for the study of enzyme inhibation and other biological activities owing to the concept that sulfonyl hydrazide moiety is an important part of different drugs.

The crystal structure of bundlin A p-bromophenylsulfonylhydrazone (Uramoto et al., 1971) has been published which contains the common moiety 4-bromo-N'-(propan-2-ylidene)benzenesulfonohydrazide which is related to the title compound (I, Fig. 1).

In (I), two molecules in the asymmetric unit are present, which differ from each other geometrically. In one molecule, the moieties of brompophenyl A (C1–C6/BR1), ethylidenehydrazine B (N1/N2/C7/C8) and ethyl acetate C (C9/C10/O3/O4/C11/C12) are almost planar with r. m. s. deviation of 0.0255, 0.0078 and 0.0398 Å, respectively. The dihedral angle between A/B, A/C and B/C is 86.14 (13)°, 54.81 (14)° and 65.35 (16)°, respectively. The sulfonyl group D (O1/S1/O2) is of course planar and makes a dihydral angle of 50.23 (21)° with its parent brompophenyl moiety. In second molecule, the similar moieties E (C13–C18/BR2), F (N3/N4/C19/C20) and G (C21/C22/O7/O8/C23/C24) are planar with r. m. s. deviation of 0.0059, 0.0016 and 0.0522 Å, respectively. The dihedral angle between E/F, E/G and F/G is 88.25 (10)°, 58.35 (14)° and 63.99 (19)°, respectively. The sulfonyl group H (O5/S2/O6) makes a dihydral angle of 58.24 (7)° with its parent brompophenyl E moiety. Both molecules are dimerized with themselves due to classical H-bondings of N—H···O type with R22(14) (Table 1, Fig. 2) ring motifs (Bernstein et al., 1995). The dimers of molecules containing bromine atom BR1 are interlinked due to C—H···O type of H-bondings, where CH is of phenyl ring and O-atom is of ester group.

Related literature top

For a related structure, see: Uramoto et al. (1971). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 4-bromobenzenesulphonohydrazide (0.251 g, 1 mmol) and ethyl acetoacetate (0.130 g, 1 mmol) in ethanol (20 ml) was refluxed for 4 h and then cooled to room temperature. After cooling, the solvent was removed under reduced pressure and the colorless solid residue was obtained. The resulting product was re-crystallized in ethanol and obtained colorless prisms of (I). m.p. 388 K.

Refinement top

The H-atoms were positioned geometrically (N—H = 0.86, C–H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = xUeq(C, N), where x = 1.5 for CH3 and x = 1.2 for other H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The partial packing, which shows that molecules are dimersed and then polymeric chains are formed. The H-atoms not involved in H-bondings are omitted for clarity.
Ethyl (3E)-3-[2-(4-bromophenylsulfonyl)hydrazin-1-ylidene]butanoate top
Crystal data top
C12H15BrN2O4SZ = 4
Mr = 363.23F(000) = 736
Triclinic, P1Dx = 1.535 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.0550 (3) ÅCell parameters from 4293 reflections
b = 11.9763 (4) Åθ = 2.0–26.0°
c = 13.1146 (3) ŵ = 2.76 mm1
α = 77.457 (1)°T = 296 K
β = 72.163 (2)°Prism, colourless
γ = 73.981 (1)°0.30 × 0.15 × 0.14 mm
V = 1571.92 (8) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6096 independent reflections
Radiation source: fine-focus sealed tube4293 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 7.80 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1414
Tmin = 0.635, Tmax = 0.650l = 1616
22120 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0612P)2 + 1.5738P]
where P = (Fo2 + 2Fc2)/3
6096 reflections(Δ/σ)max = 0.001
344 parametersΔρmax = 1.27 e Å3
0 restraintsΔρmin = 1.11 e Å3
Crystal data top
C12H15BrN2O4Sγ = 73.981 (1)°
Mr = 363.23V = 1571.92 (8) Å3
Triclinic, P1Z = 4
a = 11.0550 (3) ÅMo Kα radiation
b = 11.9763 (4) ŵ = 2.76 mm1
c = 13.1146 (3) ÅT = 296 K
α = 77.457 (1)°0.30 × 0.15 × 0.14 mm
β = 72.163 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6096 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4293 reflections with I > 2σ(I)
Tmin = 0.635, Tmax = 0.650Rint = 0.030
22120 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.05Δρmax = 1.27 e Å3
6096 reflectionsΔρmin = 1.11 e Å3
344 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.11769 (5)0.38812 (5)0.43815 (4)0.0788 (2)
S10.78563 (9)0.03587 (8)0.17990 (7)0.0411 (3)
O10.8641 (3)0.1199 (2)0.1313 (2)0.0557 (10)
O20.7263 (3)0.0035 (3)0.1162 (2)0.0558 (10)
O30.5216 (3)0.0584 (3)0.6384 (2)0.0629 (11)
O40.6201 (3)0.1478 (3)0.7100 (2)0.0532 (10)
N10.6630 (3)0.0928 (3)0.2748 (2)0.0397 (10)
N20.7025 (3)0.1166 (3)0.3597 (2)0.0384 (10)
C10.8795 (3)0.0857 (3)0.2460 (3)0.0381 (11)
C21.0045 (4)0.0849 (4)0.2421 (4)0.0544 (14)
C31.0752 (4)0.1770 (4)0.2979 (4)0.0597 (16)
C41.0203 (4)0.2686 (3)0.3560 (3)0.0461 (12)
C50.8954 (4)0.2710 (4)0.3593 (3)0.0482 (12)
C60.8250 (4)0.1790 (3)0.3030 (3)0.0453 (12)
C70.6106 (3)0.1691 (3)0.4305 (3)0.0396 (11)
C80.4704 (4)0.2101 (4)0.4284 (3)0.0586 (16)
C90.6502 (4)0.1910 (3)0.5228 (3)0.0424 (12)
C100.5890 (3)0.1252 (3)0.6290 (3)0.0419 (12)
C110.5598 (6)0.0940 (7)0.8188 (4)0.099 (3)
C120.6102 (3)0.1162 (2)0.89744 (13)0.109 (3)
Br20.35796 (4)0.36766 (4)0.06489 (4)0.0807 (2)
S20.68585 (4)0.53305 (5)0.30636 (4)0.0406 (3)
O50.60925 (4)0.63906 (5)0.34696 (4)0.0562 (10)
O60.73411 (5)0.43392 (7)0.37752 (5)0.0600 (10)
O70.99883 (6)0.64595 (9)0.14623 (7)0.0629 (11)
O80.89569 (5)0.82270 (6)0.20911 (5)0.0571 (10)
N30.81726 (5)0.56299 (7)0.21809 (5)0.0401 (10)
N40.7935 (3)0.6522 (3)0.1321 (2)0.0384 (9)
C130.5960 (3)0.4894 (3)0.2375 (3)0.0378 (11)
C140.4690 (4)0.5485 (4)0.2418 (4)0.0541 (16)
C150.3982 (4)0.5113 (4)0.1912 (4)0.0646 (16)
C160.4555 (4)0.4169 (4)0.1368 (3)0.0513 (14)
C170.5823 (4)0.3571 (3)0.1316 (3)0.0498 (14)
C180.6528 (4)0.3938 (3)0.1828 (3)0.0448 (12)
C190.8945 (4)0.6858 (3)0.0688 (3)0.0411 (12)
C201.0308 (4)0.6400 (4)0.0792 (4)0.0603 (16)
C210.8693 (4)0.7805 (3)0.0225 (3)0.0442 (12)
C220.9295 (4)0.7404 (3)0.1316 (3)0.0428 (12)
C230.9492 (6)0.7938 (5)0.3193 (4)0.088 (2)
C240.8877 (10)0.8834 (7)0.3902 (5)0.151 (4)
H10.582870.106780.273340.0476*
H21.041210.022580.201980.0649*
H31.159970.177050.296170.0714*
H50.859300.333810.398860.0579*
H60.740910.179690.303350.0542*
H8A0.465250.242670.355790.0878*
H8B0.427100.268950.475000.0878*
H8C0.428970.144840.453060.0878*
H9A0.624680.274400.527270.0511*
H9B0.744400.167160.508900.0511*
H11A0.466200.125240.835930.1181*
H11B0.575740.009930.820310.1181*
H12A0.702370.083010.881930.1631*
H12B0.568030.081270.967850.1631*
H12C0.594570.199410.895940.1631*
H3A0.894520.527370.223520.0481*
H140.431490.613080.278570.0650*
H150.312080.549930.194060.0775*
H170.619650.293000.094190.0597*
H180.738550.354390.180510.0534*
H20A1.030260.627750.154180.0903*
H20B1.082370.695880.039420.0903*
H20C1.067440.566990.050820.0903*
H21A0.903670.846040.020610.0530*
H21B0.775820.808150.012550.0530*
H23A1.042580.788180.341740.1054*
H23B0.933770.718730.321900.1054*
H24A0.794930.891680.365100.2268*
H24B0.918090.862580.461880.2268*
H24C0.908700.956380.391310.2268*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0633 (3)0.0840 (4)0.0816 (4)0.0112 (3)0.0321 (3)0.0156 (3)
S10.0424 (5)0.0425 (5)0.0351 (5)0.0108 (4)0.0027 (4)0.0082 (4)
O10.0520 (17)0.0497 (17)0.0538 (17)0.0190 (14)0.0037 (13)0.0009 (13)
O20.0610 (18)0.0643 (19)0.0442 (16)0.0064 (14)0.0166 (14)0.0179 (14)
O30.076 (2)0.073 (2)0.0516 (17)0.0494 (18)0.0108 (15)0.0003 (15)
O40.0545 (16)0.075 (2)0.0368 (14)0.0327 (15)0.0092 (12)0.0028 (13)
N10.0329 (16)0.0461 (18)0.0392 (17)0.0084 (14)0.0044 (13)0.0123 (14)
N20.0397 (17)0.0412 (17)0.0361 (16)0.0136 (14)0.0071 (14)0.0077 (14)
C10.039 (2)0.039 (2)0.0376 (19)0.0126 (16)0.0050 (16)0.0109 (16)
C20.046 (2)0.052 (2)0.067 (3)0.023 (2)0.015 (2)0.003 (2)
C30.042 (2)0.068 (3)0.073 (3)0.024 (2)0.018 (2)0.001 (2)
C40.044 (2)0.051 (2)0.045 (2)0.0073 (18)0.0155 (18)0.0092 (19)
C50.050 (2)0.049 (2)0.049 (2)0.0175 (19)0.0138 (19)0.0045 (19)
C60.039 (2)0.049 (2)0.053 (2)0.0160 (18)0.0125 (18)0.0092 (19)
C70.041 (2)0.040 (2)0.0349 (19)0.0133 (16)0.0021 (17)0.0056 (16)
C80.044 (2)0.074 (3)0.052 (3)0.000 (2)0.008 (2)0.021 (2)
C90.045 (2)0.046 (2)0.038 (2)0.0197 (18)0.0028 (17)0.0095 (17)
C100.038 (2)0.046 (2)0.043 (2)0.0148 (18)0.0075 (17)0.0068 (18)
C110.107 (4)0.164 (6)0.040 (3)0.084 (4)0.012 (3)0.012 (3)
C120.137 (6)0.154 (6)0.052 (3)0.068 (5)0.029 (4)0.002 (4)
Br20.0752 (4)0.0956 (4)0.0968 (4)0.0393 (3)0.0383 (3)0.0181 (3)
S20.0412 (5)0.0483 (6)0.0339 (5)0.0158 (4)0.0065 (4)0.0066 (4)
O50.0492 (16)0.0646 (19)0.0545 (17)0.0135 (14)0.0028 (14)0.0311 (15)
O60.0692 (19)0.0684 (19)0.0463 (16)0.0249 (16)0.0256 (14)0.0111 (14)
O70.069 (2)0.0466 (18)0.0585 (18)0.0060 (15)0.0043 (16)0.0199 (15)
O80.0664 (19)0.0519 (17)0.0427 (16)0.0043 (14)0.0066 (14)0.0082 (14)
N30.0303 (16)0.0441 (18)0.0438 (18)0.0091 (13)0.0073 (13)0.0044 (14)
N40.0411 (17)0.0359 (16)0.0374 (16)0.0107 (14)0.0044 (14)0.0095 (13)
C130.038 (2)0.040 (2)0.0370 (19)0.0138 (16)0.0103 (16)0.0019 (16)
C140.040 (2)0.054 (3)0.069 (3)0.0041 (19)0.012 (2)0.022 (2)
C150.038 (2)0.076 (3)0.084 (3)0.006 (2)0.021 (2)0.022 (3)
C160.051 (2)0.059 (3)0.054 (2)0.025 (2)0.020 (2)0.004 (2)
C170.056 (3)0.043 (2)0.055 (2)0.0112 (19)0.018 (2)0.0119 (19)
C180.041 (2)0.042 (2)0.051 (2)0.0057 (17)0.0147 (18)0.0069 (18)
C190.042 (2)0.042 (2)0.040 (2)0.0139 (17)0.0009 (17)0.0161 (17)
C200.039 (2)0.078 (3)0.063 (3)0.021 (2)0.008 (2)0.006 (2)
C210.049 (2)0.038 (2)0.041 (2)0.0146 (17)0.0016 (18)0.0097 (17)
C220.039 (2)0.042 (2)0.045 (2)0.0122 (18)0.0008 (17)0.0120 (18)
C230.105 (4)0.096 (4)0.045 (3)0.001 (3)0.009 (3)0.021 (3)
C240.223 (10)0.125 (6)0.077 (4)0.040 (6)0.060 (6)0.027 (4)
Geometric parameters (Å, º) top
Br1—C41.887 (4)C6—H60.9300
Br2—C161.901 (5)C8—H8B0.9600
S1—O21.424 (3)C8—H8A0.9600
S1—N11.636 (3)C8—H8C0.9600
S1—O11.427 (3)C9—H9B0.9700
S1—C11.766 (4)C9—H9A0.9700
S2—O61.4280 (9)C11—H11B0.9700
S2—N31.6297 (8)C11—H11A0.9700
S2—C131.765 (4)C12—H12A0.9600
S2—O51.4271 (8)C12—H12B0.9600
O3—C101.200 (5)C12—H12C0.9600
O4—C111.467 (6)C13—C181.380 (5)
O4—C101.311 (5)C13—C141.377 (6)
O7—C221.196 (4)C14—C151.375 (7)
O8—C231.462 (5)C15—C161.366 (6)
O8—C221.319 (4)C16—C171.375 (6)
N1—N21.420 (4)C17—C181.375 (6)
N2—C71.270 (5)C19—C201.492 (7)
N1—H10.8600C19—C211.496 (5)
N3—N41.409 (3)C21—C221.503 (5)
N4—C191.278 (5)C23—C241.425 (10)
N3—H3A0.8600C14—H140.9300
C1—C21.370 (6)C15—H150.9300
C1—C61.380 (5)C17—H170.9300
C2—C31.374 (7)C18—H180.9300
C3—C41.369 (6)C20—H20A0.9600
C4—C51.376 (7)C20—H20B0.9600
C5—C61.375 (6)C20—H20C0.9600
C7—C91.501 (5)C21—H21A0.9700
C7—C81.498 (6)C21—H21B0.9700
C9—C101.503 (5)C23—H23A0.9700
C11—C121.413 (7)C23—H23B0.9700
C2—H20.9300C24—H24A0.9600
C3—H30.9300C24—H24B0.9600
C5—H50.9300C24—H24C0.9600
O1—S1—O2120.04 (17)O4—C11—H11B109.00
O1—S1—N1108.05 (17)C12—C11—H11A109.00
O1—S1—C1107.54 (18)H11A—C11—H11B108.00
O2—S1—N1104.25 (19)O4—C11—H11A109.00
O2—S1—C1109.86 (19)C12—C11—H11B109.00
N1—S1—C1106.29 (17)C11—C12—H12B109.00
O5—S2—O6120.45 (5)H12A—C12—H12C109.00
O5—S2—N3107.69 (5)H12B—C12—H12C109.00
O5—S2—C13107.71 (12)C11—C12—H12A109.00
O6—S2—N3103.84 (5)C11—C12—H12C110.00
O6—S2—C13108.70 (12)H12A—C12—H12B109.00
N3—S2—C13107.84 (13)C14—C13—C18120.7 (4)
C10—O4—C11116.9 (4)S2—C13—C14119.8 (3)
C22—O8—C23116.2 (3)S2—C13—C18119.4 (3)
S1—N1—N2113.1 (3)C13—C14—C15119.4 (4)
N1—N2—C7114.7 (3)C14—C15—C16119.4 (4)
S1—N1—H1123.00Br2—C16—C17119.0 (3)
N2—N1—H1124.00C15—C16—C17121.9 (4)
S2—N3—N4114.28 (15)Br2—C16—C15119.2 (4)
N3—N4—C19115.1 (3)C16—C17—C18118.7 (4)
S2—N3—H3A123.00C13—C18—C17119.8 (4)
N4—N3—H3A123.00N4—C19—C20126.0 (4)
C2—C1—C6120.9 (4)C20—C19—C21118.9 (4)
S1—C1—C6119.6 (3)N4—C19—C21115.1 (4)
S1—C1—C2119.5 (3)C19—C21—C22113.0 (3)
C1—C2—C3119.4 (4)O7—C22—O8124.3 (3)
C2—C3—C4119.7 (4)O7—C22—C21124.4 (3)
C3—C4—C5121.4 (4)O8—C22—C21111.3 (3)
Br1—C4—C5120.7 (3)O8—C23—C24108.9 (5)
Br1—C4—C3117.9 (4)C13—C14—H14120.00
C4—C5—C6118.9 (4)C15—C14—H14120.00
C1—C6—C5119.8 (4)C14—C15—H15120.00
C8—C7—C9118.9 (3)C16—C15—H15120.00
N2—C7—C9115.2 (3)C16—C17—H17121.00
N2—C7—C8125.9 (3)C18—C17—H17121.00
C7—C9—C10112.1 (3)C13—C18—H18120.00
O4—C10—C9111.9 (3)C17—C18—H18120.00
O3—C10—C9124.1 (3)C19—C20—H20A109.00
O3—C10—O4124.0 (3)C19—C20—H20B109.00
O4—C11—C12111.3 (5)C19—C20—H20C109.00
C3—C2—H2120.00H20A—C20—H20B109.00
C1—C2—H2120.00H20A—C20—H20C109.00
C4—C3—H3120.00H20B—C20—H20C110.00
C2—C3—H3120.00C19—C21—H21A109.00
C6—C5—H5121.00C19—C21—H21B109.00
C4—C5—H5121.00C22—C21—H21A109.00
C5—C6—H6120.00C22—C21—H21B109.00
C1—C6—H6120.00H21A—C21—H21B108.00
C7—C8—H8C109.00O8—C23—H23A110.00
H8B—C8—H8C109.00O8—C23—H23B110.00
H8A—C8—H8C109.00C24—C23—H23A110.00
C7—C8—H8B109.00C24—C23—H23B110.00
C7—C8—H8A110.00H23A—C23—H23B108.00
H8A—C8—H8B109.00C23—C24—H24A109.00
C7—C9—H9A109.00C23—C24—H24B109.00
C10—C9—H9B109.00C23—C24—H24C109.00
C10—C9—H9A109.00H24A—C24—H24B110.00
C7—C9—H9B109.00H24A—C24—H24C109.00
H9A—C9—H9B108.00H24B—C24—H24C109.00
O1—S1—N1—N263.0 (3)N3—N4—C19—C21180.0 (3)
O2—S1—N1—N2168.3 (3)S1—C1—C2—C3176.9 (4)
C1—S1—N1—N252.2 (3)C6—C1—C2—C31.6 (7)
O1—S1—C1—C20.5 (4)S1—C1—C6—C5176.6 (3)
O1—S1—C1—C6178.0 (3)C2—C1—C6—C51.9 (6)
O2—S1—C1—C2131.8 (3)C1—C2—C3—C40.4 (7)
O2—S1—C1—C649.8 (4)C2—C3—C4—Br1176.2 (4)
N1—S1—C1—C2116.0 (4)C2—C3—C4—C50.4 (7)
N1—S1—C1—C662.5 (3)Br1—C4—C5—C6176.5 (3)
C13—S2—N3—N459.0 (2)C3—C4—C5—C60.1 (6)
O5—S2—C13—C147.2 (4)C4—C5—C6—C11.0 (6)
O5—S2—C13—C18174.8 (3)N2—C7—C9—C10115.5 (4)
O6—S2—C13—C14124.8 (3)C8—C7—C9—C1064.9 (4)
O6—S2—C13—C1853.1 (3)C7—C9—C10—O33.5 (5)
O5—S2—N3—N457.04 (16)C7—C9—C10—O4177.7 (3)
O6—S2—N3—N4174.17 (15)S2—C13—C14—C15177.7 (4)
N3—S2—C13—C1858.9 (3)C18—C13—C14—C150.2 (7)
N3—S2—C13—C14123.2 (3)S2—C13—C18—C17178.1 (3)
C11—O4—C10—C9176.5 (4)C14—C13—C18—C170.2 (6)
C11—O4—C10—O34.8 (6)C13—C14—C15—C160.5 (7)
C10—O4—C11—C12174.6 (4)C14—C15—C16—Br2178.9 (4)
C23—O8—C22—O70.5 (6)C14—C15—C16—C170.4 (7)
C22—O8—C23—C24171.0 (6)Br2—C16—C17—C18179.4 (3)
C23—O8—C22—C21179.7 (4)C15—C16—C17—C180.0 (6)
S1—N1—N2—C7174.9 (3)C16—C17—C18—C130.3 (6)
N1—N2—C7—C82.5 (5)N4—C19—C21—C22113.9 (4)
N1—N2—C7—C9177.9 (3)C20—C19—C21—C2266.6 (5)
S2—N3—N4—C19172.6 (2)C19—C21—C22—O75.4 (6)
N3—N4—C19—C200.5 (5)C19—C21—C22—O8174.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.462.909 (5)114
N3—H3A···O7ii0.862.362.8855 (13)120
C3—H3···O4iii0.932.533.450 (6)172
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z; (iii) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC12H15BrN2O4S
Mr363.23
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)11.0550 (3), 11.9763 (4), 13.1146 (3)
α, β, γ (°)77.457 (1), 72.163 (2), 73.981 (1)
V3)1571.92 (8)
Z4
Radiation typeMo Kα
µ (mm1)2.76
Crystal size (mm)0.30 × 0.15 × 0.14
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.635, 0.650
No. of measured, independent and
observed [I > 2σ(I)] reflections
22120, 6096, 4293
Rint0.030
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.135, 1.05
No. of reflections6096
No. of parameters344
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.27, 1.11

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.462.909 (5)114
N3—H3A···O7ii0.862.362.8855 (13)120
C3—H3···O4iii0.932.533.450 (6)172
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z; (iii) x+2, y, z+1.
 

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana Inter­national, Karachi, Pakistan.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationUramoto, M., Ōtake, N., Ogawa, Y., Yonehara, H., Marumo, F. & Saito, Y. (1971). Acta Cryst. B27, 236–241.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar

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